Hydantoin

Hydantoin is a heterocyclic organic compound that is a type of imidazolidine. It is a white solid that is slightly soluble in water and polar organic solvents. Hydantoin is used in the synthesis of other compounds, including the anticonvulsant drugs phenytoin and ethosuximide.

Chemical Structure

Hydantoin has a five-membered ring structure, with two nitrogen atoms at positions 1 and 3, and a carbonyl group at positions 2 and 4. The compound is a tautomeric compound, meaning it can exist in two forms that are in equilibrium with each other.

Synthesis

Hydantoin can be synthesized from glycolic acid and ammonia under heat and pressure. This reaction is known as the Bucherer-Bergs reaction. Another method of synthesis is the condensation of urea with glyoxal.

Uses

Hydantoin and its derivatives are used in a variety of applications. They are used in the synthesis of pharmaceuticals, especially anticonvulsant drugs such as phenytoin and ethosuximide. They are also used as plasticizers and as additives in cosmetics.

Safety

Hydantoin is not considered highly toxic, but it can cause irritation to the skin and eyes. It is not considered a carcinogen.

See Also

• Imidazolidine
• Bucherer-Bergs reaction
• Phenytoin
• Ethosuximide

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  Hydantoin synthesis pathway
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  Chemical reaction involving hydantoin
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  Iprodione chemical structure